


Earning a Bonus

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Anal Sex, Boss Castiel, Bottom Dean, CEO Castiel, Clothed Sex, Cock & Ball Torture, Desk Sex, Dominant Castiel, Employee Dean, Gags, Humiliation, Janitor Dean, Light Dom/sub, M/M, Mildly Dubious Consent, Nipple Torture, Object Insertion, Objectification, Office Sex, Older Castiel, Orgasm Denial, Pain Kink, Poor Dean, Power Dynamics, Power Imbalance, Power Play, Praise Kink, Reward, Rough Sex, Size Difference, Size Kink, Submissive Dean, Top Castiel, Twink Dean, boss/employee, mentioned castiel/other(s)
Language: English
Status: Completed
Published: 2017-06-11
Updated: 2017-06-11
Packaged: 2018-11-12 23:01:16
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,296
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11171904
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: Dean was expecting to be fired from his job, the job that was barely paying his bills, when he was called to the CEO's office after hours. He never expected Mr. Novak to offer him a bonus.But first he had to complete a performance review if he wanted the money and Dean really wanted it.





	Earning a Bonus

**Author's Note:**

> Written for a prompt.

Dean swallowed as the last of his clothing hit the floor and he shifted on his feet, aware of his boss’s eyes on his bare form. It was mercifully warm in the large office as he fought not to jerk in surprise when Mr. Novak came around the desk to circle him.

“Has anyone told you how gorgeous you are?” he asked softly, hand trailing down Dean’s back and ghosting over the swell of Dean’s ass. “Bright green eyes, pretty features, lips made to wrap around cocks and your body…so much temptation wrapped up in my janitor.”

He wasn’t sure what to stay and instead focused on the view outside the huge windows that rested behind Mr. Novak’s impressive desk. The city was lit up in the darkness, a beautiful view worthy of a CEO.

“I have a bonus for you after all the hard work you’ve done but first, as I said when you came in, we’re going to do a bit of a performance review”

Dean was quite aware of what kind of performance review his boss was talking about; it was why he was standing there completely naked while Mr. Novak wore a business suit worth more money than Dean’s apartment several times over.

“Aside from the mentioned bonus that you’ll earn after your performance review I’m increasing your pay to something to reflect your hard work.” Mr. Novak’s fingers curled around his chin and turned him so he was staring into bright blue eyes. “I reward hard work, Dean.” His voice was soft and had a shiver running down Dean’s spine at the promise he could hear in the words. “I’m very… _thorough_  when I notice potential.”

He couldn’t have held back the whimper if there had been a gun to his head. Dean watched satisfaction cross Mr. Novak's features as his face was released. He had always been turned on my authority.

“I’d like you spread out on my desk.”

Dean blinked and glanced over at the desk before walking towards it on slightly unsteady legs. Excitement and nervousness were warring inside him but the prevalent feeling was arousal.

This was wrong, very very wrong, but Dean did things that were wrong all the time.

“On your back.” Was added before he bent over the desk which was the first thing that came to him when he thought of desk sex. Dean turned around, hoisted himself up so his bare ass was pressed to the cool wood and waited as Mr. Novak closed the distance.

His body was maneuvered in the way his boss wanted him with his feet up on the desk, legs bent and hands gripping his ankles. Mr. Novak hummed and spread him out a little more so he was further exposed.

“Perfect.” He praised and Dean flushed but maintained the position. His muscles burned slightly but hearing the praise had him tightening his fingers around his ankles. “I’d love to spend hours posing and then fucking you in those positions but I have something else in mind.”

The desk drawer was opened and Dean had no idea until something was wrapped tightly around his cock. He strained to see it but from the position it wasn’t possible. Instead he groaned at the feeling of something acting like a cockring.

There was a soft pop of something opening and slick fingers rubbed against his hole. The sensation had him shivering, a soft moan escaping, as Mr. Novak rubbed more firmly and pressed the tip of his finger inside. It probed at his insides, working deeper and moving inside him with a slight burn. “You’re so hot inside.” Mr. Novak commented idly and Dean swallowed roughly. “Maybe I should change your job description? How would you feel about occasionally working in my office in a more…intimate position? Though  _positions_  might be more accurate considering how delightful you look bent like this on my desk. You could aid me in stress relief. I would pay you handsomely, of course, for each…session. It would be similar to my masseuse who comes once a week only it would be once a day. ”

 _Basically an expensive whore_ Dean thought to himself.  _I would be coming up to his office to whore myself out and then return to cleaning his building._

“You’re very good at taking instructions and obeying.” The tone of pleasure was impossible to miss.

He couldn’t really speak when Mr. Novak found his prostate and started to massage it. His breathing hitched, caught in his throat and it took everything not to move. Mr. Novak offered more praise as he began to finger him open before withdrawing. Each added finger had his ass burning with the new stretch until he had slowly adjusted to the increasing fullness.

It felt odd being empty after having three long, talented fingers moving inside him but Mr. Novak didn’t leave him empty for long. Something thick and cold pushed into him, fucked his ass a few times and stilled.

“Keep tight around it.” Mr. Novak spoke as he moved away from between Dean’s legs leaving him exposed, with something buried in his ass, to the large windows.

Dean clenched down around the object, a question on the tip of his tongue but Mr. Novak laid a finger against his lips.  His fingers started first with Dean’s left nipple, rolling it between his fingers and pinching it until Dean is whimpering, achingly hard at the delicious pain/pleasure combination he was getting from the treatment.

After a while Mr. Novak moved on to the right giving it the same treatment but it wasn’t until he had both of Dean’s nipples aching that Dean caught sight of the binder clips typically used for papers. The first one bit into his right nipple and Dean gasped, eyes slamming shut and body going tense as the binder clip viciously clamped down on him. The second one was just as jarring and his body was tight as a bowstring when both binder clips remained locked down on his nipples.

“Almost.” The voice murmured from beside him but Dean could only focus on the sensation of being full and the bright pain in both nipples.

Dean could feel hands touching him, adjusting him while he maintained his position out of pure stubbornness and an innate need to please. Mr. Novak always expected the best of his employees and Dean wasn’t going to fail.

When Mr. Novak was satisfied with the binder clips on each nipple, something wrapped tight around his cock which was taped to his stomach so it wouldn’t move and two, thick objects were buried in his ass. Mr. Novak shoved a tie that he’d removed from his desk into Dean’s mouth while another tie was wrapped around and tied to keep it secured in his mouth.

“It’s nice to see the discipline you put into your job reflected now.” A hand stroked him before the sound of a zipper caught his attention. “Most employees who receive a special bonus can’t quite follow every instruction so perfectly during their performance review. I’m pleased I caught sight of you this morning.”

There were a few more noises that escaped Dean and then the objects inserted into his ass were being removed. He gasped at the feeling and clenched around nothing. Blurry eyes blinked open to see Mr. Novak staring at him with open lust and interest, smile curling his lips.

“You can let go for now.” Dean’s fingers flexed and moved until he was moving closer to the edge of the desk. Once more he was guided but this time he was gripping his legs behind the knees to keep his body bent, legs spread and hole offered. “Good. You’re so good for me. You take care of my building and now you’re taking care of me.”

The cock that pushed into him was thicker than the objects he’d held in his ass and the burn of it stretching him open further had a whimper escaping. A gasp punched out of him when suddenly Mr. Novak had buried himself balls deep in a quick, hard thrust. 

“You feel so good around my cock, Dean. Warm and tight, gripping me perfectly. Such a hard worker.” Mr. Novak drew back and gave a sharp snap of his hips to bury himself inside once more. “ _Fuck_.” It was hissed when Dean tightened down at the feeling of his boss’s cock striking against his prostate before Mr. Novak started up a quick pace. “You’re absolutely perfect like this. If I had known I would have given you a bonus in person before tonight.”

Balls slapped against him with each snap of Mr. Novak’s hips and every time his prostate was nailed Dean had to struggle to keep his position. Dean wanted to wrap his legs around his boss’s waist for a more comfortable position but this was the position he’d been instructed to maintain. “ _Please_.” He wasn’t completely aware of what he was asking for, only that he needed to but the tie muffled his words. “ _Please_.” Dean’s breathing shuddered and a whimper escaped when the cock working inside him slammed deeper.

The thrusts picked up, harder and harder, until Mr. Novak’s pace fell off and his movements became erratic. The slap of skin on skin was filthy along with deeply pleasured moans and grunts when each balls deep thrust.

Dean could tell he was getting close to his orgasm and when it hit, Mr. Novak slamming deep and stilling, his head banged against the desk and a whimper escaped at the denial of his own orgasm.

A warm hand stroked his cheek, a finger thumbing over his silk covered lips before Dean felt Mr. Novak pulling out and disposing of his condom in the trash nearby. “Don’t worry.” He murmured, “I’ll let you come after I fuck your perfect ass against the window for everyone to see.”

Dean flushed as he moved into the position he was directed into, once more with his feet firmly planted on the desk and his hands gripping his ankles. Fingers probed at his sensitive hole and once more objects were inserted into him. He wished he could see what Mr. Novak was pushing inside of him but his position prevented it.

“I’ll have to make sure I have a better supply in my office next time. Clearly you are more than capable of more and I want to cultivate that innate talent into something that shines.” Mr. Novak teased his balls with something soft that dragged up the underside of Dean’s restrained cock. “My office lacks certain necessities…we might have to continue this meeting further at my home. I think your ass would look gorgeous cherry red and split open on one of larger dildos I use to entertain with.”

Dean gasped when another object was worked into his hole. He had no idea what his boss was pushing inside but his hole was starting to ache.

“After a good fucking against the window, of course.”

His breathing hitched and his body warmed as Mr. Novak’s palm cradled his balls. Dean’s eyes were closed and his body was tight, tense and poised, as a pleased sigh escaped his boss.

“I love using the smallest binder clips for this.” Then something sharp was pinching violently into the skin of his balls. Dean jerked, body tensing and mouth falling open on a moan of pain, as more sharp pinches started to register on his balls. “Nothing like a little ball torture between fucks.”

Dean’s cheeks were flushed and his breathing ragged, as small binder clip after small binder clip clamped onto the sensitive skin of his balls.

Mr. Novak released his balls, humming in satisfaction, before digging around in his desk again. Dean panted, fingers tight and body twitching. Then the tape was being removed from his cock and tight bands were wrapped around the length of him.

“It’s a _decent_ size...if you like them short.” Mr. Novak commented as he stood between Dean's legs, “What are you? Three? If I'm generous...four inches?” Dean flushed with humiliation. He had caught sight of Mr. Novak’s thick cock and it was easily nine or ten. His was shorter and plump. He knew what his boss was doing. “These rubber bands might be tight…”

One ended up directly underneath the head of his cock, tight and breath stopping, before Mr. Novak was satisfied.

“I don’t keep toys in my office but I have found so many creative ways to use office supplies.” Dean could only lie there on the desk, body tense after the denial of his release and the mixture of pain/pleasure his boss was inflicting upon him with clear experience. Tape once more secured his cock to his stomach. “How someone like you became a janitor.” Mr. Novak shook his head, “You would make more as a high-end whore and your looks wouldn’t be wasted.”

Dean flushed as his boss idly touched him, watching with clear appreciation and hands roaming over his body in fascination.

“Their loss.” He murmured and another object was pushed into his aching hole. “You’re doing so well, Dean. So well. At this rate your bonus might be bigger than it was when you walked in the door.”

He could only hope it was. Dean was barely scraping by, bills killing him and any kind of extra money would go a long way to helping him keep his head above water financially.

Dean thought about his boss’s words, the comment about the money he could make as a high-end whore, and silently saved it away. He knew whoring could be a good way to make money, he knew it, and even with this bonus he would need the money.

**Author's Note:**

> The whole office supply thing was very different but who doesn't like variety? It is, as they say, the spice of life haha.
> 
> Hope you all liked this one! It was different so I'm sure that was a nice little treat for some of you.


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